A mountainous landscape with autumn foliage.

Stephens City Holiday Rentals

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Our top choices for Stephens City holiday rentals

1. Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (12 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
The price is NZ$313
includes taxes & fees
13 Sept - 14 Sept
Luxury tiny home farm stay on historic property with hot tub in Stephens City

2. Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
8.8 out of 10, Excellent, (10 reviews)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
United States
Anonymous traveller
Cozy English Basement Apt quiet but close to downtown

3. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (37 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is NZ$368
includes taxes & fees
27 Aug - 28 Aug
Mountain View Bungalow in Front Royal

4. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is NZ$328
includes taxes & fees
25 Aug - 26 Aug
Rosamond nice downtown studio apt

5. Chalet w/Hot Tub, Deck, Game Room & EV Charger

Chalet w/Hot Tub, Deck, Game Room & EV Charger
Stephens City
10.0 out of 10, Exceptional, (7 reviews)
Chalet w/Hot Tub, Deck, Game Room & EV Charger

6. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Winchester Historic District
10.0 out of 10, Exceptional, (2 reviews)
"The unit is very nice, exactly as described, The bed are comfortable and everything was fine. The location is excellent very near to historical sights and downtown shopping district."
United States
Timothy B.
The price is NZ$443
includes taxes & fees
20 Aug - 21 Aug
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

7. The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
7.0 out of 10, Good, (2 reviews)
"Everything went smoothly. Easy stay. Clean. Small efficiency with futon for bed."
United States
Greg A.
The price is NZ$337
includes taxes & fees
14 Sept - 15 Sept
The Stock Exchange downtown 3rd floor studio apt

8. The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.6 out of 10, Good, (8 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The price is NZ$470
includes taxes & fees
20 Aug - 21 Aug
The Queen of Winchester Three Bedroom with Upper Level Deck

9. Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.6 out of 10, Exceptional, (9 reviews)
"It was decorated very cute and the bed was comfortable. Very close to shops and restaurants.We had to drive around the block and get out to find the location because you park and enter through the back door.It’s very close to the train stain but was only interrupted by an early morning train once."
United States
Brenda H.
The price is NZ$366
includes taxes & fees
30 Aug - 31 Aug
Pretty Little Apt by the Train II

10. Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.4 out of 10, Very good, (6 reviews)
"Loved being so close to the old town; was able to walk to a lot of places. Great to have an assigned parking spot in a lot behind the building. Enjoyed staying here a lot!"
United States
Leslie L.
The price is NZ$391
includes taxes & fees
31 Aug - 1 Sept
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

11. Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
Old Town Winchester
7.6 out of 10, Good, (4 reviews)
"You need to add some kitchen tongs Otherwise everything was fantastic!!!"
United States
Michelle K.
The price is NZ$430
includes taxes & fees
15 Sept - 16 Sept
Yellow Submarine trendy basement apt and courtyard

12. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.6 out of 10, Exceptional, (9 reviews)
"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."
United States
Carolyn F.
The price is NZ$582
includes taxes & fees
20 Aug - 21 Aug
Cameron Charmer pristine downtown apt with double master suites

13. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.2 out of 10, Wonderful, (18 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
The price is NZ$555
includes taxes & fees
20 Aug - 21 Aug
Nostalgia Lane in the heart of the city

14. Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Old Town Winchester
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is NZ$415
includes taxes & fees
31 Aug - 1 Sept
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

15. Indigo Blue modern open vibe on tree lined street

Indigo Blue modern open vibe on tree lined street
Winchester Historic District
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! The place was very clean and exactly as described. Michele communicated clearly and responded quickly, which made everything easy from check-in to check-out. The location was also perfect—very close to downtown and convenient to everything we wanted to do. We would definitely stay here again and highly recommend it to others!"
United States
Elaina R.
The price is NZ$686
includes taxes & fees
23 Aug - 24 Aug
Indigo Blue modern open vibe on tree lined street

16. WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Old Town Winchester
9.0 out of 10, Wonderful, (10 reviews)
"Great location…"
United States
John P.
The price is NZ$619
includes taxes & fees
30 Aug - 31 Aug
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

17. Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Old Town Winchester
The price is NZ$544
includes taxes & fees
31 Aug - 1 Sept
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

18. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (15 reviews)
"Unique and adorable little place on the river. Perfectly clean and comfortable. We would definitely book again!"
United States
Hailey
The price is NZ$734
includes taxes & fees
20 Aug - 21 Aug
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

19. Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is NZ$669
includes taxes & fees
23 Aug - 24 Aug
Scarborough Fair walk to downtown two story apt

20. Bend of Brothers’ | Riverfront Cottage Shenandoah

Bend of Brothers’ | Riverfront Cottage Shenandoah
Front Royal
8.0 out of 10, Very good, (1 review)
"This is a new place and owners have done great work . Excellent value for the money ."
United States
Dave B.
The price is NZ$628
includes taxes & fees
20 Aug - 21 Aug
Bend of Brothers’ | Riverfront Cottage Shenandoah
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Stephens City Hotel Reviews

Find out more about Stephens City

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Stephens City holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Stephens City. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Stephens City. Seeing all the best attractions is bound to make you fall in love with Stephens City. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Stephens City short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Stephens City?

Yes, there are holiday rentals in Stephens City close to Appleland Sports Center, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Stephens City has a good selection of restaurants. Make sure you have time to check out the shopping and wineries during your trip.

What are some of the best holiday rentals that Stephens City has to offer?

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub: This holiday home rental outside of Stephens City is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Stephens City?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Stephens City stay.

What’s there to see and do in Stephens City?

While exploring the area, visit family-friendly sights like Appleland Sports Center, or get outside and enjoy nature at Lake Frederick Boat Launch. In the wider area, you’ll find Valerie Hill Winery and Dinosaur Land.

What’s a holiday rental in Stephens City like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stephens City. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.